Brooke and Jeffrey: Second Date Update - Second Date Update: Bobby 2.0

Episode Date: August 31, 2026

Bobby didn’t come across in the best way the FIRST time he was on our show, but this time he SWEARS he’s changed and is now deserving of our help with a Second Date Update! See omnystudio.com/listener for privacy information.

Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat the veggies? Will the pasto survive the first bite? Will the lunchbox come home empty, half full, or come home at all? And will you finish episode 8 before you're done slicing the cucumbers? Get Bell Pure Fiber Internet with Craved Netflix and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit. Visit bell.com for details and to check availability.

Bell, connection is everything. If your bookshelf and your for you page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your favorite writers, book talk creators, and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I survived nine months in captivity, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are the Survivor Files.

Every week, I'm with survivors who live through the unthinkable, abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to the Survivor Files with Elizabeth Smart on the IHeart Radio app, Apple Podcast, or wherever you get your podcasts. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinero and I travel by myself because it's a rare space where I can say yes without asking anyone else first.

I'm on a mission to reclaim the word Solita, trading the pity for possibility. Listen to Solita on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, this is Hayes Davenport. And Sean Clements. We host the podcast, Hollywood Handbook. Each week, we talk to someone in show business and try to help them with their careers and see what they have to offer us. Everyone has a good time, and no one gets mad at their publicists for letting them do our show. We've had a lot of great guests like Sarah Sherman, Adam Scott, Danny McBride, Ben Stillard,

and a lot of other big shots that wouldn't be where they are without us. Listen to Hollywood Handbook on the I Heart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's Brook and Jeffrey in the morning. And, you know, we get all the credit for all these second dates going viral. Yeah. But really, it's our listeners and their terrible dating decisions that we have to think. Yes. And the people who ghost people.

Yes. Helping us out. Thank you. Your toxicity has made us so funny. Yes. So thank you. Hey, don't forget, we do have 45 more minutes of this. We've got a full show over on the Brook and Jeffrey main feed.

if you'd like it, follow that one as well. And let's get into your second date. Brooke and Jeffrey in the morning. Second date update. Today we have a guy named Bobby, who was actually on the show last year for a different segment called Say Yes to the X. Oh, goodness.

Oh, really? I guess she said no. Yeah, that's probably a good guess, Alexis. He told us he wanted to get back with his ex-girlfriend, but once she was on the phone, we learned he mainly just wanted to, to get back his Netflix password from her.

That's right. Oh, I remember that. Oh, and also he admitted something else to us. We had a real connection and I don't think that we need to give up on it so quickly.

You have a girlfriend again already. What the hell, Bobby? Ashley was just way less complicated. You know, dating this new chick for like 72 hours and it's just already a lot. Oh.

I remember. Bobby's a winner. Bobby was messy. I remember that about Bobby. So yeah, he came on to say yes to the ex, but also already had a new girlfriend at the time. Yeah. But according to Bobby's latest email, he says he has grown quite a bit from that experience.

Either that or all the women heard that and dumped him. That's growth in some ways. And he needs our help today, this time with a second date update. So let's welcome back the new and improved Bobby. Wow. Bobby 2.0. Bobby, welcome back, man. How you doing?

Hey, man, honestly, just hearing that clip, I was really going through it back then. It was kind of weird to hear. Bobby, how many girlfriends have you had since we last talked to you, bro? I don't know exactly. I don't have a list or anything, but I mean, I'm like, I'm not just trying to reach out to people to get Netflix passwords anymore. I got a lot of my friends, give me some crap, give me some guff. Yeah, well, you're kind of using people. It didn't come off real well when you were on our show last.

Yeah, I took some time off of dating after that, honestly. I took like a whole week, I think I took off. Wow. I mean, you were lying about this personal growth, Jeff. You practically took a sabbatical. Yeah. We're all extremely impressed by you, Bobby. And it's a pleasure to have you back on.

Since that week, though, it's been like Times Square looking for a prize, man. It's been Time Square? Time Square? What does that mean, loud? Beautiful, bright, shiny people all around. You know what I mean? That square's like the worst part of the city is. It's crowded around here.

Is that a good thing? I can't tell. Is Times Square a good thing? I think it's supposed to be. Brooke, I think he's trying to use it as an analogy. Yeah, I understand the analogy. There's a lot of people that go through and you're trying to find the one in the crowd. You know there's something there.

I just feel like he enjoyed it. That's all I'm trying to get at. But that's fine. Brooke is not an English major and doesn't know how metaphors and similes work. I just think it wasn't a good one. Disagree. Bobby, you're a poet. Keep going.

Tell us about the new and improved you and how you met someone. So, yeah, after all the flashing lights and all the distractions, I found, I met this girl, Mandy. I met her in a pottery class. Oh, that's like the Central Park of dating. Wow. I get the analogy. Let's leave the analogies to Bobby.

Go ahead, Bobby. Yeah, what happened? How are you in a pottery class, Bobby? Good question. Well, I heard it was a good place to meet women. Oh, that's how you're right. Okay. So I talked to this girl and her friend, and I said,

do you guys know anything about pottery? Can you help me out? Play dumb out of boy. Aren't you in a class? Like a cooking class. They're like trying to enjoy their time and have to help a man who can't do it himself. This teacher doesn't know what the hell they're talking about. Can you explain it to me?

Did that actually work? Yeah. So in the end, they were both like laughing at me and how terrible my base was. But then, you know, she kind of, Mandy kind of hung around after. And we were talking. And Mandy's friend was getting ready to leave. And then that's when I invited Mandy to go to this ice cream place that was right next door to the pottery spot. Okay.

Oh, that's smooth. Did you know? Did you know they make non-dairy ice cream? Yeah. Yeah. It's good. Yeah. It's called bad ice cream.

It's like this whole place, it was like plant-based ice cream. Oh, gross. Possible ice cream, Jeff. Don't trigger him. Did you like it? Well, she had something she called California Cabin and it, it tasted like wood, honestly. She gave me a little. Oh, wow.

It was a little bit of wood in it. I had cookies and cream, strawberry cookies and cream, actually, and minus the cream. And actually, actually, that was pretty badgum delicious. Sounds delicious. Okay. All right. So what about, what about? What about you and Mandy?

How is your connection? I mean, we hung out just to eat an ice cream. We finished our ice cream. We were probably 20, 30 minutes of us just talking. And then I told her, I said, hey, so this doesn't really count as a date. We should have an official one. That's cute. Oh, nice.

She seemed open to it. Uh-huh. And then we were going over options for, like, when to meet, what to do. and she couldn't really decide or she seemed busy. I couldn't tell, but we never got anything together. Okay. Back in Times Square all over again. Yeah.

Yeah, back to Times Square, exactly. So you left it at what? I mean, I texted her a couple times to try and talk, but she hadn't responded at all. And I mean, this is kind of weird for me. Normally, like, it's not usually this tough to meet up with somebody. Okay. Did you go back to the pottery class or was that a one-off?

So I've been to the beginner class like three times. And the instructor kind of took me aside And was like, yo, you can't keep doing the beginner If you're going to come back You've got to move up to the intermediate class Oh Because there was more women in the beginner Is that what was going on?

I think I just didn't want to commit fully Like it feels like I'm actually Still back to that Bobby, huh? Yeah Seems like a common theme for you Yeah I mean I can commit to a beautiful woman Not pottery

Okay so how long has it been Since you last had that ice cream date? Like three weeks, almost a month. Whoa. Oh, it's been a long time. Yeah, I mean, I've reached out to her a couple times. I don't want to come off weird and clear. Like, this is new territory for me.

I kind of meant more like, do you have a current girlfriend or you do? I do not have a current girlfriend or anybody. Like, that's old me. Okay. And your Netflix password, your Hulu, everything's up to. Oh, yeah. They're wasted for now. You can't even share accounts.

I got everything I need. I'm full. I'm content. The one thing that you're missing in your life is a little. Mandy. So let's see if we can bring her back when we call her and get you a second date update pottery edition right after this. Hold on. Brook and Jeffrey in the morning. Second date update. We're on the phone with Bobby 2.0, who has grown and become a better man since his last appearance on our show. Hey, he's better Bobby. Sure is. His last time he was trying to get his

Netflix password back from his ex-girlfriend. That kind of went up in flame. Well, because he was also trying to date his ex-girlfriend while he currently had a girlfriend. Yeah. I mean. Those are just details. Yeah, a little juggling, actually. Point is, he's seen the air of his ways, and today he's trying to get in touch with a woman named Mandy, who he met at pottery class. They had some flirtatious pottery talk, ate some non-dairy ice cream together, and we're even discussing a second meetup when, just like Bobby's clay vase, everything collapsed.

Wow. And now he hasn't heard from Mandy. in almost three weeks. Doesn't know what exactly went wrong, and he's come to us seeking those answers. Bobby, did I miss anything there? I think you got it. I'm curious, where is your base that you made?

What did you put it? I think it's in my garage. Hey, you aren't even proud of it. I see. No, it was bad. I knew it was bad. I was kind of, you know. Yeah.

Put it in your cave of shame. That's why he keeps going back to the beginner course, guys. Yes. He's improving in many different ways, not just in love, but in pottery, too. So let's see if we can accomplish that first one for you. I'm going to dial Mandy's phone number. We'll see if she answers the phone, and then hopefully she can clear everything up for us. You ready to do this?

Right on. Here we go. I'm dialing it right now. Hey, Mandy. Thank you for answering. We're a radio show, by the way. You should know you're on with Brooke and Jeffrey in the morning. Wait.

Number one with pottery lovers. We're a big pottery show. I'm sorry, what? We do as the wheel turns. Yeah. Yeah. And we're really killing it. I like that.

With the jokes. Please don't hang up, Mandy. Please. Glazed right over her. Okay. Oh, no. Yes. Oh, no.

Enough. Okay. Oh, gosh. Mandy. I'm sorry. Who? I know. Who is this?

I know. I know. It's very embarrassing to admit that I'm a part of this show. And we know about the pottery stuff because we're doing a segment called a second date update. We heard you're in pottery class from a guy that you went out with. or met at Pottery. His name is Bobby. Oh, wait, that was all, like, a little while ago.

Right. We spoke to Bobby about it. He said the two of you met at that class, and then you hung out for ice cream, and he texted you a few times since, but you seem to be avoiding him. Yeah, I am avoiding him. Oh, that's clear.

Straightforward. Is it because he made fun of your ice cream for being, like, wood-flavored? No. No, no, no, no. Like, I actually, honestly, like, I thought he was kind of, like, dumb, charming for a little bit. But I mean, that makes sense. But that's kind of endearing because I think his goal really was to strike up a conversation with you.

I mean, yeah. Like, I don't need to go out with the smartest guy, but I do want to go out with a guy that is different than him. What do you mean? Okay. What did he do that was so dumb to you? Well, actually, this was pretty dumb. Like we were chatting. It was fine.

It was good. And at the end, he was like, we should hang out again. Yeah. And I was like, yeah, yeah. That sounds great. So he goes, cool. Let me get you on the calendar. Oh, wow.

That felt weird. I don't think so. Yeah. Well, I thought he was just going to like find it. Like, I used my calendar, you know? Like, I thought he was going to find a time, like, put me in his calendar. So he doesn't forget. That's good.

But then he texts me a link. And he tells me to open in front of him. And it's a link to a booking calendar. like where I can schedule my date and time with him. Like a spreadsheet. I'm still trying to picture what you're saying. Maybe he's just really type A and everything's super organized. I'm imagining one of the links it takes you to and you're trying to make a dentist appointment.

It's like 3 p.m. on Tuesday a month somehow. Wouldn't that be a good sign that he's got his stuff organized? No, because it doesn't end there. Like you open up the booking calendar and it says, congrats, you've been selected to book a date with Bobby. Sponsored Limited, so act fast. Oh, this is a specific dating booking calendar. Yeah, it's a dating booking calendar.

Oh. Wait, wait. Did he laugh when you opened it because he wanted you to open it right there? So maybe it's like a joke. No, he did not laugh. He was completely serious about this. Oh, God. And then the next prompt, it says, like, who's booking?

And then it has a list of, like, eight different girls' names. Oh, it's a drop-down list. Oh, no. Oh, my God. the plot. I wanted to see like how this process works, you know. So I click the link and I go in and then I find out he's

charging people. What? What do you mean charging people? He's charging people. It says you can book an appointment for $75. Oh my God. What? That is so much money. Who does he think he is? It's pretty smooth, actually.

$75 just to like see this man. Alexis is like, wait, I could have done this the whole time. to pay for your half of the date. Does that mean that seven other women paid the $75? That means every woman, I guess, who's on his calendar,

presumably has paid $75. If they're real. Wow. If they're real booking. This man, he is a genius and I wish I could tell him it myself. And luckily I can because he's on the phone right now listening to this conversation.

Yeah, for free. Why didn't we charge him? Has he been listening this whole time? Yeah, that's the other part of how this works, Mandy, as we have them listening on the other line. But Bobby, are you there? Yeah, I don't see the problem. I told you guys I've grown. I'm definitely way more

organized. That's not the girl who are wanting from you, Bobby. Oh, my gosh. It is very impressive, Bobby. I'll say that, but you could also see how it might be a turnoff to a woman who you just met where you're sending her to a calendar and showing her all the other options

of women that you have. And charging her, Jeff. The charging her. That part I kind of like. I mean, Look, if I were her, you know, I'd take it to the challenge. Like, this guy's wanted, there must be something special about them. Okay. Oh. What do you think about that, Mandy?

Okay, wait, so were those women not real? Like, did you make them up? No, absolutely not. That's why I was so confused by all this because normally, whenever I give them the calendar, they book immediately. This is the first time I've actually had to work. Like, I'm calling the radio, you know? I care about this. I care about, you know, I'm trying to make it happen.

Wow. You're the caring guy in this? You didn't call us about any of the other women on his list. That's true. Because they're not real. I still don't believe it. Dude, $75 is a really high fee. It's called you get what you pay for.

I'm just making sure that I'm not wasting my time. They put a little bit of something in it too. That means that they got a little skin in the game. You know what I mean? That actually makes sense. Bobby, how would you feel if maybe came to you with this, right? I mean, if the rolls were reversed, first, I'd be impressed. Second, I would probably ask for a little bit of a discount, you know, because I'm a catch.

And I think that I could probably work something out. So wait. What I'm hearing, Mandy, he's opened a negotiation. If the price point is the problem, we could work with that. All right, we're starting at $74. $74. There's not a need for that. Look, I've already put in a promo code.

It's just Bobby. You just put it in 50% all. Wow. This guy is moving mountains for you right now. Are you seeing what I'm seeing? Um, no, not really. Oh, man. I mean, Bobby, talk directly to her.

I feel like it needs to be like your elevator pitch. You know, we're in a business transaction at this point. Mandy, if I hadn't showed you my calendar and how organized that and how on top I am of all my stuff, then you would have probably gone out with me? Yeah, yeah, probably. That's ridiculous, man. Women complain that they want a man who communicates, who's a planner. I go and do all of this. And I get punished because I'm really good with ladies.

This is a joke, dude. I don't understand it. Oh, wow. Because he's good. Is that really how you read this? I mean, we're running out of time here, so Bobby made his pitch. What's wrong with women? Bobby is so different than the last time we talked to him.

Wow. At this point, he's really running out of time is Mandy, because this is not going to last forever. These spots are going to get chilled up. Only two slots available left, Mandy. So now's your chance. Would you go out on another date with Bobby? I'm going to throw it out there. And if you say yes, we would be so generous as to pay the fee to get you booked.

Wait, we're going to pay the $32 and $32 and $32. No, Brooke, the math is $37 is half. Not 32. Come on, Brooke. Brooke, what's wrong? Are you trying to shortchange me? This money goes directly to my streaming services, and that's not cheap. That's right, because you can't share the passwords anymore with your ex.

I get it. Sorry, Bobby. Let this man have is Netflix. And Mandy, it's up to you. Do you want to see him one more time? You know what? My booking calendar is full now. So unless you want to pay me $75, I'm not going to be.

Whatever. I got a couple spots, though. Brooke, do you want to fill a spot? I'm good. She'll say yes off air. Look, Jeff and I are in tight. I'll just send him the link. And Jeff, you send it to Brooke.

I knew he wouldn't ask Alexis because she couldn't afford that. Oh, wow. That's very accurate, actually. He was great. Brooke and Jeffrey in the morning. Today's episode is brought to you by Vinted. And if you guys are anything like me, my style changes with every season.

I love keeping up with trends, but I'll go from loving one style to suddenly wanting a completely different wardrobe just a few weeks later. And I definitely don't want to spend a ton of money every few months. And that's why I've started using Vinted. Vinted is a secondhand app

that makes it easy for everyday sellers, people like you and me, to sell pre-loved fashion and earn some extra money. So thanks to Vinted, What I've started doing is going through my closet, finding clothes I'm not wearing anymore, and selling them on Vinted. It's really quick and simple. You just list your item by taking a few pictures of it.

And when it sells, Vinted sends you a prepaid shipping label. Plus, there's no seller fees, so you keep everything you earn. Then you can cash out your money or what I like to do, use it right on Vinted to find some new clothes. That way, I can refresh my wardrobe without feeling like I just spent a ton of money. So I get to clear out my closet, make some money, and find new pieces I actually love all on Vinted. If you're ready to clean out your closet and make some extra money, download the Vinted app for free and start listing. With no seller fees, you keep every dollar you earn.

Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat the veggies? Will the pastos survive the first bite? Will the lunchbox come home empty, half full, or come home at all? And will you finish episode 8 before you're done slicing the cucumbers? Get Bell Pure Fiber Internet with Craved Netflix and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit.

Visit bell.ca for details and to check availability. Bell, connection is everything. Why do I have a feeling Bobby 3.0 is going to make an appearance on this show in the next six to 12 months? Oh, my God. I think it's because he's one of the most unself-aware people that we've ever had. So I believe that he will be back. I'm with Jeff. Yeah.

Or should we tell our producer to put him on our official block list? No, he's entertaining. Let's take a vote on it. Alexis, yay, nay, or hey neighbor to Bobby 3.0. I don't understand hey neighbor. You're giving a hey neighbor? Yes, that's what I heard. Brooke?

Hey neighbor. Jose? I say, yay. All right. The yays and hey neighbors have it. We're going to let them back. It's something to look forward to. Like a present in the middle of Times Square, as Bobby would say.

Give them a yay neighbor collective. I love everybody shouting hey neighbor with us. Texan hey neighbor if you want to. That's right. And also email the show if you need help with your Love life. We can call that person who's not calling you back. Go check out all of our second day podcasts are up online wherever you get yours at Brooke and Jeffrey. On the new podcast Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinero and I travel by myself because it's a rare space where I can say yes without asking anyone else first.

I'm on a mission to reclaim the word Solita, trading the pity for possibility. Listen to Solita on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, this is Hayes-Davenport and Sean Clements. We host the podcast, Hollywood Handbook. Each week, we talk to someone in show business and try to help them with their careers and see what they have to offer us. Everyone has a good time, and no one gets mad at their publicists for letting them do our show. We've had a lot of great guests like Sarah Sherman, Adam Scott, Danny McBride, Ben Stillard and a lot of other big shots that wouldn't be where they are without us.

Listen to Hollywood Handbook on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your for-you page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island to serve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your favorite writers, book talk creators, and plenty of overthought opinions. I'm obsessed. I'm obsessed.

Listen to Pro Society on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I survived nine months in captivity, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are the Survivor Files. Every week, I'm with survivors who live through the unthinkable, abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to the Survivor Files with Elizabeth Smart on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Our hometown is not a test tube. 90 miles northeast of Nashville, a battle for the future of America plays out in one small town.

Developers with right-wing ties have purchased hundreds of acres of land. We need cities on a shining hill. This is our town, a podcast about what happens. when a small town becomes the sight of a social experiment and fights back. Guess you didn't move in on a bunch of dumb hillbillies now, did you? Listen to Our Town on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.